Photobactericidal plastic films based on cellulose esterified by chloroacetate and a cationic porphyrin.
The synthesis and characterisation of pyridinium porphyrinic chloroacetyl cellulose ester chlorides, where photosensitizing agents are covalently bounded to the polymeric chain, is presented in this paper. First, cellulose was homogenously converted into chloroacetate cellulose ester in DMAc/LiCl solvent by using chloroacetyl chloride. The complete substitution of cellulose was achieved using 7equiv of chloroacetyl chloride for a 2h reaction at room temperature. The absence of base did not prove detrimental to reaction. The grafting of monopyridyltritolylporphyrin onto chloroacetate cellulose ester was then realised by alkylation of the photosensitizer in DMF. These new plastic films were found to be thermostable up to 55 degrees C; higher temperatures led to progressive deacetylation. First results of their photobactericidal activity against Staphylococcus aureus and Escherichia coli strains are very encouraging. Such materials could find applications in medical environments as an alternative to overcome the rampant bacterial multiresistance to classical antibiotics.
Krouit
Mohammed
M
Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123, Avenue Albert Thomas, 87060 Limoges cedex, France.
Granet
Robert
R
Krausz
Pierre
P
D000085:Acetates / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002482:Cellulose / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D004951:Esterification; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology*; D010969:Plastics / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000085:Acetates; D000900:Anti-Bacterial Agents; D004952:Esters; D017319:Photosensitizing Agents; D010969:Plastics; D011108:Polymers; D011166:Porphyrins; C006972:chloroacetic acid; D002482:Cellulose; C045557:chloroacetyl chloride